Travel Expectations — Enjoying the Unexpected

Andrew LaRussa
Digital Global Traveler
4 min readAug 15, 2023
Photo by Artem Maltsev on Unsplash

Growing up, I always struggled with going on a trip and not enjoying it. All because I had expectations for what I wanted to do on the trip. But when those things don’t happen, I get disappointed. Regardless of the fun things I have done on the trip, I would still be disappointed. This was because I grew up with a brother with Aspergers. We had to do everything he wanted to do first so he wouldn’t have a meltdown. So before we left on the trip he got to pick two things he wanted to do and we would do them first. Then my parents had the things they wanted to do and usually, they thought that we would enjoy it too. But in the end, I would be left disappointed by what I never got to do.

When I got old enough to do the things I wanted by myself. I would still set expectations and still get disappointed. But I finally realized if you find one thing that you want to get out of the trip and aim for that. You can meet your expectations. In the end, you can then enjoy everything unexpected that unfolds around you. This is easier said than done though. It has given me the opportunity to meet some amazing people. it has also given me some very rewarding adventures over the last few years.

Photo by Allen Taylor on Unsplash

Back in 2013, I went to San Francisco on Valentine’s Day with a girl for a day trip. I had recently started embracing the unexpected. All I planned was dinner and that was it. But as we walked around the city we heard people talking about an event that night. We didn’t hear what it was or even where. But everyone was talking about something big. Later that night we were walking back to the car to head home and passed 3 people carrying pillows. They handed them to us and told us to have fun. Come to find out, every Valentine’s Day there is a massive pillow fight in a square near the Embarcadero. We stumbled across it, and I embraced the unexpected and jumped into the middle of it. There had to be about 300 people and I literally jumped into the middle of it. A pillow fight in downtown San Francisco is something I will never forget to this day.

I have found that expectations either never live up to what we have in our heads, or we can never meet them. Then we are disappointed even when we have had amazing experiences. So we never enjoy the little things in life. I’m not saying don’t have expectations. Expectations in relationships like finding a good person that treats you with respect. It is a much-needed expectation in our lives. But when those expectations are broken, then you need to walk away.

Having some patients is hard for a lot of people. But wondering the streets and starting random conversations with strangers. This has given me some of the most amazing memories. But planning every minute of your day allows for disappointment. It doesn’t give room to allow the chance for unexpected adventures. My friend always says he never says no when he is out. I try to embrace this mindset, but I also have to remember the limits to this though. Nothing extremely dangerous or illegal. Like drugs or things of that nature, and we have to live in a realm of money, so can I afford it? If someone is willing to pay for it, then let us do it.

This has been something on my mind and I know I have not mastered it yet, but I find I am getting better with it. I know a camping trip during the pandemic was a prime example of this. But I had low expectations and they were never met and I honestly still consider the trip a failure. My only expectation was to relax and get out of my own head a bit. Others around me had different plans. But I am still learning, and hopefully, someone else will try this as well. It’s something I plan to keep practicing though, and someday to be much better at.

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Andrew LaRussa
Digital Global Traveler

One half of a bi-national marriage, American and South African, looking to take the world my storm. Freelance photographer and inspiring freelance journalist.